Non‐Covalent Assembly Method that Simultaneously Endows a Liposome Surface with Targeting Ligands, Protective PEG Chains, and Deep‐Red Fluorescence Reporter Groups

Scott K Shaw; Wenqi Liu; Seamus P Brennan; María de Lourdes Betancourt‐Mendiola; Bradley D Smith

doi:10.1002/chem.201702649

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Non‐Covalent Assembly Method that Simultaneously Endows a Liposome Surface with Targeting Ligands, Protective PEG Chains, and Deep‐Red Fluorescence Reporter Groups

Journal article

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Non‐Covalent Assembly Method that Simultaneously Endows a Liposome Surface with Targeting Ligands, Protective PEG Chains, and Deep‐Red Fluorescence Reporter Groups

Scott K Shaw, Wenqi Liu, Seamus P Brennan, María de Lourdes Betancourt‐Mendiola and Bradley D Smith

Chemistry : a European journal, Vol.23(51), pp.12646-12654

09/12/2017

DOI: 10.1002/chem.201702649

PMCID: PMC5961722

PMID: 28736857

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Abstract

A new self‐assembly method is used to rapidly functionalize the surface of liposomes without perturbing the membrane integrity or causing leakage of the aqueous contents. The key molecule is a cholesterol‐squaraine‐PEG conjugate with three important structural elements: a cholesterol membrane anchor, a fluorescent squaraine docking station that allows rapid and high‐affinity macrocycle threading, and a long PEG‐2000 chain to provide steric shielding of the decorated liposome. The two‐step method involves spontaneous insertion of the conjugate into the outer leaflet of pre‐formed liposomes followed by squaraine threading with a tetralactam macrocycle that has appended targeting ligands. A macrocycle with six carboxylates permitted immobilization of intact fluorescent liposomes on the surface of cationic polymer beads, whereas a macrocycle with six zinc(II)‐dipicolylamine units enabled selective targeting of anionic membranes, including agglutination of bacteria in the presence of human cells. Decoration without disruption: Insertion of a cholesterol‐squaraine‐PEG conjugate into the outer leaflet of a pre‐formed liposome followed by macrocycle threading of the squaraine component produces a functionalized deep‐red fluorescent liposome.

cell recognition

fluorescent probes

liposomes

membranes

supramolecular chemistry

Details

Title: Subtitle: Non‐Covalent Assembly Method that Simultaneously Endows a Liposome Surface with Targeting Ligands, Protective PEG Chains, and Deep‐Red Fluorescence Reporter Groups
Creators: Scott K Shaw - University of Notre Dame
Wenqi Liu - University of Notre Dame
Seamus P Brennan - University of Notre Dame
María de Lourdes Betancourt‐Mendiola - University of Notre Dame
Bradley D Smith - University of Notre Dame
Resource Type: Journal article
Publication Details: Chemistry : a European journal, Vol.23(51), pp.12646-12654
DOI: 10.1002/chem.201702649
PMID: 28736857
PMCID: PMC5961722
NLM abbreviation: Chemistry
ISSN: 0947-6539
eISSN: 1521-3765
Number of pages: 9
Grant note: Directorate for Mathematical and Physical Sciences (CHE1401783) National Institute of General Medical Sciences (R01GM059078; T32GM075762)
Language: English
Date published: 09/12/2017
Academic Unit: Chemistry
Record Identifier: 9984216589802771

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